Dichloromethane → 2,4-Dichloro-6-methoxymethyl-3-nitro-pyridine

HRID 1724852Notes

Reaction equation

HRID 1724852 reaction equation
[CH3:1][O:2][CH2:3][C:4]1[N:9]=[C:8](O)[C:7]([N+:11]([O-:13])=[O:12])=C(O)[CH:5]=1.O=P(Cl)(Cl)[Cl:17].[CH2:20]([Cl:22])Cl>>[Cl:17][C:8]1[C:7]([N+:11]([O-:13])=[O:12])=[C:20]([Cl:22])[CH:5]=[C:4]([CH2:3][O:2][CH3:1])[N:9]=1

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 24813Phosphorus oxychlorideHCID 178494546HCID 178494546, compound

Product 1

HCID 575611042,4-Dichloro-6-methoxymethyl-3-nitro-pyridine

Procedure

6-Methoxymethyl-3-nitro-pyridine-2,4-diol (725 mg, 3.63 mmol) is added to a solution of POCl3 (15 mL) at 0° C. The mixture is warmed to room temperature followed by heating at reflux for 5 hours. Excess POCl3 is removed under reduced pressure to yield a light brown oil. The crude oil is dissolved in CH2Cl2 (100 mL) and extracted with water (100 mL), NaHCO3 (100 mL), and brine (100 mL). The organic extract is dried over Na2SO4 and the solvent removed under reduced pressure. The crude product is chromatographed on silica gel eluting with hexanes/EtOAc (4:1) to yield the title compound as a light yellow oil.

Workup

  1. temperatureby heating
  2. temperatureat reflux for 5 hours
  3. customExcess POCl3 is removed under reduced pressure
  4. customto yield a light brown oil
  5. extractionextracted with water (100 mL), NaHCO3 (100 mL), and brine (100 mL)
  6. extractionThe organic extract
  7. dry with materialis dried over Na2SO4
  8. customthe solvent removed under reduced pressure
  9. customThe crude product is chromatographed on silica gel eluting with hexanes/EtOAc (4:1)

Sources & evidence

ORD record
ord-5a2cc6647e724560b6188c800d1d5df4
Source dataset
uspto-grants-2009_02
Patent number
US07488740B2

Reaction notes

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